Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
  • C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes

Definitions

• This invention relates to a process for the alkylation of secondary aliphatic amines, consisting of reacting a secondary aliphatic amine with at least one hydrogen on the alpha carbon atom of the amino group with a compound containing at least one olefinic unsaturation, in the presence of a particular type of catalyst.
• Secondary aliphatic amines, tertiary aliphatic amines, particularly of long chain, and the quaternary ammonium salts easily obtainable therefrom are of notable importance. All these compounds are used as such mainly as surface active agents, some of which are biodegradable. They are also used in the textile industry as antistatic or softening agents, as wetting agents and as dye fixers. In the pharmaceutical industry they are used as bacteriostatic agents or bactericides, and as ganglionolithic agents. More generally, they may be used in the flotation of certain minerals, as additives for emulsifying asphalts and as oil additives in the form of corrosion inhibitors. They are used in the paint industry as pigment dispersing agents, and in certain cosmetic preparations as additives.
• the compounds in question are also widely used in the chemical industry as intermediates in the preparation of interesting derivatives.
• secondary aliphatic amines are used in the synthesis of enamines, which on polymerization produce auxiliary products for the textile industry and for the production of plastics.
• This very wide range of applications thus makes secondary aliphatic amines and their derivatives of great interest.
• up to the present time there have been difficulties in their synthesis.
• Their synthesis from petroleum cuts gives rise to considerable disadvantages in addition to the need for multi-stage processes.
• the present invention provides a process for the alkylation of secondary aliphatic amines comprising the reaction between a secondary aliphatic amine with at least one hydrogen on the alpha carbon atom of the amino group, and a compound containing at least one olefinic unsaturation, preferably an olefine itself, in the presence of a catalyst consisting of an amide of a transition metal, of formula
• R is alkyl, aryl or cycloalkyl
• n is the valency of the metal
• M is the metal itself, which as stated belongs to the transition metal series and is preferably chosen from Ti, Zr, Hf, V, Nb, Ta, Cr, Mo and W.
• the catalyst may be added to the reaction environment already formed, or may be obtained in situ by adding a salt of the transition metal to the amine concerned. It is evident that in this case the amido radical which becomes bonded to the metal derives from the secondary aliphatic amine which is to be alkylated.
• the reaction takes place at a temperature of 100°-250° C. in the presence of an aprotic solvent.
• aprotic solvent e.g., benzyl alcohol, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzylene, glyma, diglyma, tetrahydrofuran, pyridine, and chloroform are particularly useful.
• Reaction is continued at 160° C. for 8 hours under magnetic agitation.
• the mixture is reacted at 170° C. for 10 hours under agitation.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Applications Claiming Priority (2)

Publications (1)

Family

ID=11224167

Family Applications (1)

Country Status (9)

Cited By (33)

Families Citing this family (3)

Citations (11)

• 1976
  • 1976-10-28 IT IT28778/76A patent/IT1068433B/it active
• 1977
  • 1977-09-07 US US05/831,241 patent/US4110377A/en not_active Expired - Lifetime
  • 1977-09-16 CH CH1136877A patent/CH626321A5/it not_active IP Right Cessation
  • 1977-09-20 GB GB39218/77A patent/GB1578238A/en not_active Expired
  • 1977-10-24 FR FR7731953A patent/FR2369243A1/fr active Granted
  • 1977-10-26 NL NL7711767A patent/NL7711767A/xx not_active Application Discontinuation
  • 1977-10-27 JP JP12821477A patent/JPS5356602A/ja active Pending
  • 1977-10-27 DE DE2748293A patent/DE2748293C3/de not_active Expired
  • 1977-10-28 BE BE182192A patent/BE860281A/xx not_active IP Right Cessation

Patent Citations (11)

Non-Patent Citations (1)

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